Getting Outlook’s Calendar into iCal for the iPhone

As I understand it, iTunes for Windows allows you to sync your iPod – or more importantly (these days) your iPhone – with Outlook for contacts and calendar items. That seems well and good for Windows users I suppose, but not so for my co-worker and his new iPhone. (Unfortunately for him I’m a bigger Apple nerd than he, and the phrase, “Can I see your iPhone?” has become an old joke very quickly…)

You see my friend and I work in a place – like many, many places – that uses Microsoft’s Exchange server for email, thus Outlook is the tool of choice for email, contacts, calendars, etc. The issue my co-worker faces is that he syncs his iPhone with his Mac at home, not his work PC. Thus, his work-based calendar items (which don’t exactly translate on the poor IMAP/Exchange integration) aren’t loaded onto his iPhone. (And between you and me, He misses enough meetings as it is…) So what to do?

As most of my friends do when they have an Apple related question, he came bugging me (which was only fair given the love affair I’ve had with his iPhone). I should mention also that he’s a senior engineer (hence the missed skipped meetings) and doesn’t like to do a lot of ‘heavy lifting’, so the process of exporting a CSV from Outlook each day to mangle into iCal was out of the question – Can you blame him?
So we did some digging. Finally, we came to a solution in the form of Plaxo. Plaxo is the plugin for Outlook that many of you may have gotten invites to a few years back when it came on the scene, and all your co-workers and friends wanted you to jump off a bridge join up too. Well in its current manifestation it’s a much more full-featured (and free!) plugin, which in the Beta 3.0 version rocks a pretty slick web-based hub. This web-hub acts as a one-stop-shop for all your calendar and contact needs (as well as much more) and imports from Outlook of course. But the real magic comes in to play with the ability to sync several different services to this one-stop web-hub. iCal, Google Calendar, Yahoo Calendar, and on and on and on can all share their info to the website, which syncs it between all the sources, in effect unifying your contacts and scheduled appearances. Brilliant!

So now you’ve got Plaxo keeping all parties up to date – a new item in iCal updates to Plaxo, which then updates to Outlook (and Google Calendar, and Yahoo, and so on) and vis versa. So no matter where a new item is added, all apps from end to end get the memo. Thus, the end game of getting Outlook calendar items onto a Mac-based/sync’d iPhone is a success.

A footnote to this, is that obviously those appointments are only made available to the iPhone when a sync to iTunes (and in turn, iCal) is performed. As Plaxo plays so nicely with all these other services, Google Calendar (which got a nice iPhone/Safari makeover) for instance, is updated on the fly and immediately available for calendar updates in between hard syncs with the Mac!

So there you have it. All you Mac and iPhone users stuck trying to integrate with the world of Microsoft can hopefully get on a little easier now. Many thanks to my buddy for letting me spend so much quality time with his iPhone, and having a fun and interesting story to show for it. Hopefully he doesn’t pummel me for all the slacker references…

As I’ve been typing this, the thought occurred that it may be possible to sync the iPhone with multiple iTunes – hence grabbing Outlook calendar entries from a Windows-based iTunes, and syncing music and everything else from an OS X-based iTunes. Does anyone know if that’s possible? If you’ve got a different (more elegant?) solution to the problem, lets hear it!